TY - JOUR
T1 - Photocatalytic Oxidation of Sulfinates to Vinyl Sulfones with Cyanamide-Functionalised Carbon Nitride
AU - Meyer, Andreas Uwe
AU - Lau, Vincent Wing hei
AU - König, Burkhard
AU - Lotsch, Bettina V.
N1 - Funding Information:
A. U. M. is funded by the Fonds der Chemischen Industrie for a doctoral scholarship, and V. W.-h. L. is funded by the Max Planck Society for a post-doctoral scholarship. This work was supported by the Deutsche Forschungsgemeinschaft (GRK 1626, Chemical Photocatalysis; LO1801/1-1), the Max Planck Society, the Cluster of Excellence Nanosystems Initiative Munich (NIM) and the Center for Nanoscience (CeNS). We would like to thank Dr. Rudolf Vasold (University of Regensburg) for his assistance with the GC–MS analysis.
Funding Information:
A. U. M. is funded by the Fonds der Chemischen Industrie for a doctoral scholarship, and V. W.-h. L. is funded by the Max Planck Society for a post-doctoral scholarship. This work was supported by the Deutsche Forschungsgemeinschaft (GRK 1626, Chemical Photocatalysis; LO1801/1-1), the Max Planck Society, the Cluster of Excellence Nanosystems Initiative Munich (NIM) and the Center for Nanoscience (CeNS). We would like to thank Dr. Rudolf Vasold (University of Regensburg) for his assistance with the GC?MS analysis.
Publisher Copyright:
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/4/18
Y1 - 2017/4/18
N2 - The cyanamide-functionalised carbon nitride (NCN-CNx) can be employed as a photo-redox catalyst for the light-induced sulfonylation of alkenes with sulfinate salts, attaining product yields twice those obtained with the non-functionalised counterpart and comparable to those achieved with the benchmark homogeneous photocatalyst Eosin Y. NCN-CNx as a heterogeneous photocatalyst is easily isolatable and can be re-used for this reaction for over three cycles. This photocatalytic reaction can proceed with various sulfinates (aryl-, alkyl- and thiophene-based) and alkenes with electron-donating and -withdrawing groups, obtaining good to excellent product yields. A reductive quenching route was determined to be the likely mechanism for this photocatalyst.
AB - The cyanamide-functionalised carbon nitride (NCN-CNx) can be employed as a photo-redox catalyst for the light-induced sulfonylation of alkenes with sulfinate salts, attaining product yields twice those obtained with the non-functionalised counterpart and comparable to those achieved with the benchmark homogeneous photocatalyst Eosin Y. NCN-CNx as a heterogeneous photocatalyst is easily isolatable and can be re-used for this reaction for over three cycles. This photocatalytic reaction can proceed with various sulfinates (aryl-, alkyl- and thiophene-based) and alkenes with electron-donating and -withdrawing groups, obtaining good to excellent product yields. A reductive quenching route was determined to be the likely mechanism for this photocatalyst.
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U2 - 10.1002/ejoc.201601637
DO - 10.1002/ejoc.201601637
M3 - Article
AN - SCOPUS:85013345375
SN - 1434-193X
VL - 2017
SP - 2179
EP - 2185
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 15
ER -